Ethanol → 1-(4-Bromophenyl)cyclobutane-1-carboxylic acid

HRID 338395Notes

Reaction equation

HRID 338395 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:12]#N)[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[OH-:14].[K+].CC[OH:18]>O.C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:12]([OH:18])=[O:14])[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 201116081-(4-Bromophenyl)cyclobutanecarbonitrile

Product 1

HCID 167699191-(4-Bromophenyl)cyclobutane-1-carboxylic acidYield 79%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-(4-bromophenyl)cyclobutanecarbonitrile (1.0 g, 4.2 mmol) in EtOH (28 mL) and water (2 mL) was added KOH (2.1 g, 42 mmol). The reaction mixture was heated to reflux for 16 hours. The reaction was then quenched with 1M hydrochloric acid in order to adjust pH to 7. The organic solvents were removed in vacuo to give a residue, which was dissolved in ethyl acetate (40 mL), then washed with brine (3×10 mL). The organic phase was concentrated in vacuo, and the resulting oil was purified by flash chromatography on silica gel (petroleum ether/ethyl acetate=8:1) to give 1-(4-bromophenyl)cyclobutanecarboxylic acid (0.8 g, 79% yield) as a white solid.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 16 hours
  3. customThe reaction was then quenched with 1M hydrochloric acid in order
  4. customThe organic solvents were removed in vacuo
  5. customto give a residue, which
  6. washwashed with brine (3×10 mL)
  7. concentrationThe organic phase was concentrated in vacuo
  8. customthe resulting oil was purified by flash chromatography on silica gel (petroleum ether/ethyl acetate=8:1)

Sources & evidence

ORD record
ord-17a26f997c2c40908d3a5e55c854d700
Source dataset
uspto-grants-2014_11
Patent number
US08889730B2

Reaction notes

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